The Greatest Advisor For You – Make Every Moment Count.

The face-off Monday night between Hillary Clinton and Donald J. Trump is, for good reason, among the most highly anticipated presidential debates in American history.

1. Will Trump call Clinton “Crooked Hillary”?

One of Trump’s most memorable and consistent — if un-presidential — tactics has been his lacerating sobriquets for his opponents. But Trump seems to be undecided about the wisdom of calling Clinton “Crooked Hillary” to her face. The No. 4 question on a “TRUMP Debate Preparation Survey,” sent out in a Sept. 16 fundraising email, was: “Do you think Trump should refer to Hillary as ‘Crooked Hillary’ on stage? Yes; No; No opinion; Other, please specify.” One wonders if “please specify” means he’s soliciting for additional nicknames.

2. Will Holt keep the candidates on track?

Holt was the lead moderator in January’s Democratic primary face-off in South Carolina among Clinton, Sanders and Martin O’Malley (remember him?). And he earned high marks for giving the candidates room to engage with each other while also keeping the debate moving along. However, the Democrats at that stage of the race were fairly civil to one another, certainly much more so than their Republican counterparts. While Holt has interviewed Trump for Nightly News,he’s never had to contend with him in a debate setting. (NBC News did not get the chance to moderate a planned GOP primary debate in February; after sister network CNBC’s debate drew howls of protest from the candidates, the Republican National Committee pulled the debate from NBC News and gave it to CNN.) The new format for presidential debates, instituted in 2012, calls for the moderator to be less intrusive and facilitate back and forth between the candidates. But observers note that this actually makes the moderators’ job harder. “The moderator is now in a position to ask follow-ups and more importantly generate a give-and-take between the candidates, which is more work for the moderator,” notes Lehrer.

3. Will Clinton fact-check Trump’s birther lies?

It’s unclear whether Holt plans to bring up Trump’s documented role in fanning the false birther conspiracy surrounding President Obama’s birth certificate. Holt on Sept. 19 revealed three very broad topics for the debate: America’s Direction, Achieving Prosperity and Securing America. But Trump has brought the issue to the fore once again; less than two weeks ago he brazenly blamed Clinton for igniting the birther issue during the bitter 2008 Democratic primary race between Clinton and Obama. Many expect Clinton to bring it up, and Robby Mook, Clinton’s campaign manager, signaled as much when he told CNN New Day anchor Alisyn Camerota on Sept. 21 that Trump “doesn’t often tell the truth.” So Clinton is “going to have to spend some time probably correcting the record and making sure voters understand the facts.”

4. How will the gender dynamic play out?

Trump has alienated wide swaths of women voters with his history of misogynistic language. So he’ll have to carefully calibrate his attacks on Clinton or risk turning her into a sympathetic figure and potentially solidifying doubts many women already have about him. His criticism of Carly Fiorina offers an object lesson in what not to do. Trump gave an interview last year to Rolling Stone in which he said: “Look at that face! Would anyone vote for that?” He tried to backtrack at a primary debate last year. But Fiorina was able to score points when she stoically declared: “I think women all over this country heard very clearly what Mr. Trump said.” Clinton has a 24-point lead among likely female voters (58 percent to 34 percent), according to a McClatchy-Marist poll released Sept. 23.

5. What’s at stake for the media?

There has been much working the refs in the run-up to debate. Trump has been accusing the moderators of being in the tank for Clinton, predicting that Anderson Cooper will be “very biased” and accusing Holt of being a Democrat who is part of a “phony” and “very unfair system.” (New York voter registration records show that Holt has been a registered Republican since 2003.) Obama has criticized the media for grading Trump “on a curve,” echoing other Clinton surrogates. But that narrative also is one that some in the media have conceded. “For a Trump statement to make news right now it would have to be so outrageous and so un-informed because there have been so many statements like that from the past,” notes Brendan Nyhan, a political science professor at Dartmouth College. “It’s impossible to deny that Trump is benefiting from the low expectations he faces.” And in a bitterly partisan era, the media has apparently hit a nadir in the estimation of consumers. According to a Sept. 14 Gallup poll, only 32 percent of Americans say they “trust the media to report the news fully, accurately and fairly,” the lowest level since Gallup began polling in 1972. How TV news anchors handle the debates will, for many, serve as a referendum on the state of the industry.

The spectacle of it alone is alluring: one of the world’s most famous women onstage for 90 commercial-free minutes alongside one of the country’s most recognizable men, in the ultimate convergence of celebrity and politics.

But with a presidential race that once seemed to be tipping in Mrs. Clinton’s favor growing more competitive as early voting begins, the debate at Hofstra University in New York is far more than a made-for-TV moment.

Here is what to look for as the candidates try to motivate — or reassure — supporters and win over a small group of undecided voters:

Can Trump demonstrate he’s fit for the Oval Office?

With a showman’s flair for generating publicity and a firebrand’s talent for touching the rawest of nerves, Mr. Trump has effectively harnessed the angst of many in the country who are not feeling the effects of the economic upswing, have tired of prolonged wars or have grievances about a changing country.

But surveys show that a majority of Americans still believe he is unqualified to be president. If Mr. Trump is to convince those voters who have doubts about his fitness for high office, but are uneasy with Mrs. Clinton, the three debates represent his best opportunity to prove he can be trusted to serve as a head of state. He has to show discipline when it comes to how he engages Mrs. Clinton, challenging her without belittling her, and at least show he is conversant on foreign and domestic policy issues.

Just as Ronald Reagan did in 1980 and George W. Bush did in 2000, Mr. Trump faces a threshold test about whether he is up to the job. But neither Mr. Reagan nor Mr. Bush faced the same level of doubt as Mr. Trump does today. The provocateur must show he can be a president.

Can Clinton hide her contempt for her opponent and her disbelief at being locked in such a close race?

It is no stretch to believe that in her internal monologue — and perhaps in intimate conversations — Mrs. Clinton wonders how she could possibly be locked in a competitive contest with a casino executive turned reality TV personality who has never run for office and has no foreign policy experience. But if Mrs. Clinton betrays any such incredulity, she risks bringing what she may think is the unthinkable that much closer to reality.

Whether it is with her body language, her tone or her words, Mrs. Clinton cannot appear contemptuous of the voters for considering the star of “The Apprentice” for the office of Washington, Jefferson and Lincoln. Just as Mr. Trump will undermine his prospects if he hurls insults at Mrs. Clinton, she must mask her contempt for him and persuade, not scold, voters. She needs only to ask Al Gore about how effective eye-rolling and sighing are when contending with an opponent you can barely believe is on the same stage.

Can Trump perform for an extended period of time without a net?

If Mrs. Clinton must guard against condescension, Mr. Trump has to worry about being exposed to a global audience as devoid of all but bluster. During the Republican primary race, he benefited from sharing a stage with numerous rivals, each of whom was eager for the airtime during a season in which Mr. Trump thoroughly dominated television news. Since his campaign’s low point this summer, when he was criticized for frequently taking it off script, Mr. Trump has put aside his mockery of politicians who use teleprompters and read from prepared text at even some of his most informal events.

But Mr. Trump now lacks safety in numbers on the stage. And when he looks into the camera Monday evening, there will be no well-chosen words for him to read. He must summon the stamina to engage fully for 90 minutes and the knowledge to answer to a battery of policy questions from both the moderator, Lester Holt of NBC, and Mrs. Clinton. A long silence, a mistaken guess or an angry dismissal all would serve to reinforce one of his biggest vulnerabilities: that he knows next to nothing about substance.

Issue with voters, especially those who remain on the fence?

Mrs. Clinton has seen her advantage in the race erode in part because she is having difficulty locking in voters who should otherwise be hers. Just take a look at how many young voters are now indicating in polls that they support one of the third-party candidates or at the hostility the remaining undecided voters have toward Mr. Trump.

As Mrs. Clinton has conceded, she must appeal to this portion of the electorate with an affirmative case for herself — not only slashing attacks on Mr. Trump. To win them over, she will need a ready answer when the inevitable question comes about her use of a private email server as secretary of state.

This moment presents an opportunity for her to not only address the narrow matter of her emails, but to offer an acknowledgment to on-the-fence voters that she has heard their concerns about her trustworthiness. She must show self-awareness about the perceptions of her character and the view that she personifies the detested political class. Mrs. Clinton may be uncomfortable hanging a lantern on her problem, to borrow a Robert Kennedy phrase, but it would signal to reluctant, would-be supporters that she has heard their concerns.

How will the moderator perform under close scrutiny?

The two candidates will not be the only ones under the microscope at Hofstra: Mr. Holt is likely to face the sort of scrutiny rarely seen of debate moderators. With his willingness to breezily tell untruths, Mr. Trump presents a unique challenge to all journalists covering the campaign. But having to hold him accountable in real time while millions across the world watch is a burden of a different order of magnitude.

Mr. Holt cannot waver when Mr. Trump dissembles. But the NBC anchor also must be careful to not become argumentative and let Mr. Trump make him the story, evading the substance at hand. At the same time, Mr. Holt has to aggressively press Mrs. Clinton and scrutinize her record and past statements.

Finding this balance — holding a norm-breaking politician to account while also not seeming to go any easier on his conventional opponent — would be difficult under the best of circumstances. But the pressure on Mr. Holt to control the stage has been heightened by the much-criticized performance from his NBC colleague, Matt Lauer, at a televised candidate forum this month. And there is something else adding to the weight on Mr. Holt: the presidency is on the line.